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Encyclopedia > Promethazine
Promethazine
Systematic (IUPAC) name
N, N-dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
Identifiers
CAS number 60-87-7
ATC code D04AA10 R06AD02, R06AD05
PubChem 4927
DrugBank APRD00601
Chemical data
Formula C17H20N2S 
Mol. mass 284.425 g/mol
Pharmacokinetic data
Bioavailability 88% absorbed but after first-pass metabolism reduced to 25% absolute bioavailability
Protein binding 93%
Metabolism Hepatic glucuronidation and sulfoxidation
Half life 16-19 hours
Excretion Renal and biliary
Therapeutic considerations
Pregnancy cat.

C(AU) C(US) Image File history File links Image is drawn in bkchem and Open Office Drawing by Bjarte Sorensen. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Atomic mass 14. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... BIC pen cap, about 1 gram. ... The mole (symbol: mol) is the SI base unit that measures an amount of substance. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Many drugs are bound to Blood plasma proteins. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in some animals, including vertebrates (and therefore humans). ... Example of glucuronidation Glucuronidation of alcohols and acids Glucuronidation is a major inactivating pathway for a huge variety of exogenous and endogenous molecules, including drugs, polluants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids and bile acids. ... A sulfoxide is a chemical compound containing a sulfinyl functional group with a sulfur oxygen double bond attached to two carbon atoms. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... It has been suggested that Renal anomalies and Renal plasma threshold be merged into this article or section. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Constitutional monarchy (federal)  - Queen Elizabeth II  - Governor-General Michael Jeffery  - Prime Minister John Howard Independence from the UK   - Constitution 1 January 1901   - Statute of Westminster 11 December 1931... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

P(UK) -only(US)
(injection POM(UK)) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... A prescription drug (or POM Prescription Only Medicine, in UK) is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Routes Oral, rectal, IV, IM

Promethazine is a first-generation H1 receptor antagonist antihistamine and antiemetic medication. It is a prescription drug in the United States, but is available over the counter in the United Kingdom, Switzerland, and many other countries (brand names Phenergan®, Promethegan®, Romergan). In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Four 500mg acetaminophen/paracetamol suppositories A suppository is a medicine that is inserted either into the rectum (rectal suppository) or into the vagina (vaginal suppository) where it melts. ... Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Intramuscular injection is the injection of a substance directly into a muscle. ... An antihistamine is a drug which serves to reduce or eliminate effects mediated by histamine, an endogenous chemical mediator released during allergic reactions, through action at the histamine receptor. ... An antiemetic is a drug that is effective against vomiting and nausea. ... A prescription drug (or POM Prescription Only Medicine, in UK) is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... Over-the-counter substances, also abbreviated OTC, are drugs and other medical remedies that may be sold without a prescription and without a visit to a medical professional, in contrast to prescription only medicines (POM). ...


Promethazine also has strong anticholinergic and sedative effects. Previously it was used as an antipsychotic, although it is generally not administered for this purpose now; promethazine has only approximately 1/10 of the antipsychotic strength of chlorpromazine. An anticholinergic agent is a member of a class of pharmaceutical compounds which serve to reduce the effects mediated by acetylcholine in the central nervous system and peripheral nervous system. ... The term antipsychotic is applied to a group of drugs used to treat psychosis. ... Chlorpromazine was the first antipsychotic drug, used during the 1950s and 1960s. ...

Contents

Indications

  • As sedative/hypnotic
  • For preoperative sedation and to counteract postnarcotic nausea
  • As antiallergic medication to combat hay fever, allergic rhinitis, etc. To treat allergic reactions it can be given alone or in combination with oral decongestants like (pseudo-)ephedrine.
  • Together with codeine or dextromethorphan against cough
  • It can be used to increase the activity of opioids. It allows lower opioid doses and decreases their emetic properties.
  • For severe Morning sickness - as an older drug with a greater experience of use during pregnancy, it is generally preferred to newer agents.
  • As a motion sickness or seasickness medication. Commonly known as the "Coast Guard cocktail" when used with Ephedrine or Pseudoephedrine.
  • As an antipruritic (pruritus vulvae).

A sedative is a substance which depresses the central nervous system (CNS), resulting in calmness, relaxation, reduction of anxiety, sleepiness, slowed breathing, slurred speech, staggering gait, poor judgment, and slow, uncertain reflexes. ... For the play, see Hay Fever. ... A decongestant is a broad class of drugs designed to symptomatically treat ailments affecting the respiratory system. ... Codeine (INN) or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. ... Dextromethorphan (DM or DXM) is an antitussive drug that is found in many over-the-counter cold and cough preparations, usually in the form of dextromethorphan hydrobromide. ... An opioid is a chemical substance that has a morphine-like action in the body. ... Morning sickness, also called nausea and vomiting of pregnancy (NVP) or pregnancy sickness, affects between 50 and 95 percent of all pregnant women as well as some women who take birth control pills or hormone replacement therapy. ... Motion sickness is a condition in which the endolymph (the fluid found in the semicircular canals of the inner ears) becomes stirred up, causing confusion between the difference between apparent perceived movement (none or very little), and actual movement. ... Seasickness is hazardous for scuba divers Seasickness is the feeling of nausea and, in extreme cases, vertigo experienced after spending time on a craft on water. ... A Coast Guard cocktail is a prescribed combination of drugs used to combat seasickness. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Pseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. ... An itch (Latin: pruritus) is a sensation felt on an area of skin that makes a person or animal want to scratch it. ...

Contraindications

  • Promethazine should not be given to children under two years of age; there is potential for fatal respiratory depression in this age group.
  • Hypersensitivity to Phenothiazines
  • Closed angle glaucoma
  • Intoxication with alcohol or other central depressants
  • Severe hypotension or shock
  • Coma due to any reason
  • Severely impaired liver function
  • Urine hesitancy due to enlargement of the prostate gland

In medicine, hypoventilation exists when ventilation is inadequate to perform gas exchange. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... In medicine, a coma (from the Greek koma, meaning deep sleep) is a profound state of unconsciousness. ... Male Anatomy The prostate is a gland that is part of male mammalian sex organs. ...

Side effects

Typical side effects are: Adverse effect, in medicine, is an abnormal, harmful, undesired and/or unintended side-effect, although not necessarily unexpected, which is obtained as the result of a therapy or other medical intervention, such as drug/chemotherapy, physical therapy, surgery, medical procedure, use of a medical device, etc. ...

  • Blurred vision
  • Confusion in the elderly
  • Drowsiness, dizziness, fatigue, more rarely vertigo
  • Dry mouth
  • Seizures (extremely rare)
  • Malignant neuroleptic syndrome (extremely rare)
  • Respiratory depression in patients under age of 2 and in those with severely compromised pulmonal function
  • Constipation

Preamture ejaculation Strange Paedophillic urges Vertigo, sometimes called a headrush, is a major symptom of a balance disorder. ... This article is about the medical condition. ... Neuroleptic malignant syndrome (NMS) is a life-threatening, neurological disorder most often caused by an adverse reaction to neuroleptic or antipsychotic drugs. ...


Dosage

Depending on disease and clinical condition (age, liver function):

  • Mild to moderate cases of agitation: 25–50 mg orally, 3 to 4 times daily
  • Insomnia: depending upon severity, 25–100 mg orally at bedtime

In pediatric patients doses as low as 5–10 mg, 3 times daily may suffice. For precise dosing syrup forms exist.


As an anti-emetic:

  • Adult: 6.25 mg IV, or 12.5 mg IM
  • Pediatric (greater than 2 years old): 0.25 mg/kg IV/ IM

Laboratory examinations

All patients should have their blood pressure measured frequently. During long-term therapy, blood cell counts, liver function studies, EKG, and EEG are recommended. The intervals should be determined according to the risk profile of the patient. A sphygmomanometer, a device used for measuring blood pressure. ... ECG may also refer to the East Coast Greenway Lead II An Electrocardiogram (ECG or EKG, abbreviated from the German Elektrokardiogramm) is a graphic produced by an electrocardiograph, which records the electrical voltage in the heart in the form of a continuous strip graph. ... EEG can mean: Electroencephalography - the method and science of recording and interpreting traces of brain electrical activity as recorded from the skull surface or the device used to record such traces Emperor Entertainment Group - A Hong Kong entertainment company. ...


External links

  • Letter from Wyeth Pharmaceuticals to practitioners regarding use of Phenergan in under twos. (PDF format)

References

  • Basic and Clinical Pharmacology, 9th ed (2004). Katzung, Bertram G. pp. 264–265.


Antihistamines (primarily R06) edit
Aminoalkyl ethers:

Bromazine, Carbinoxamine, Clemastine, Chlorphenoxamine, Diphenylpyraline, Diphenhydramine, Doxylamine An antihistamine is a drug which serves to reduce or eliminate effects mediated by histamine, an endogenous chemical mediator released during allergic reactions, through action at the histamine receptor. ... A section of the Anatomical Therapeutic Chemical Classification System. ... Ethers can refer to: In internet routing, the term associated with hosts In Organic chemistry, the plural of ether This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ... Carbinoxamine is an antihistamine. ... Clemastine is an over-the-counter antihistamine sold in the United States under the name Tavist. ... Diphenylpyraline is an antihistamine. ... Diphenhydramine hydrochloride (trade name Benadryl®, as produced by Pfizer or Dimedrol outside the US) is an over-the-counter (OTC) antihistamine and sedative. ... This article or section may be confusing or unclear for some readers, and should be edited to rectify this. ...

Substituted alkylamines:

Brompheniramine, Chlorphenamine, Dexbrompheniramine , Dexchlorpheniramine, Dimetindene, Pheniramine, Talastine Categories: Stub | Antihistamines ... Chlorphenamine (INN) or chlorpheniramine (USAN, former BAN), commonly marketed as its salt chlorphenamine maleate (CPM), is first-generation antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria. ... Dexbrompheniramine maleate is an antihistamine used to treat allergic conditions such as hay fever or urticaria. ... Dexchlorpheniramine maleate (Polaramine®, Schering) is an antihistamine used to treat allergic conditions such as hay fever or urticaria. ... Pheniramine maleate is an antihistamine used to treat allergic conditions such as hay fever or urticaria. ...

Substituted ethylene diamines:

Chloropyramine, Histapyrrodine, Mepyramine, Methapyrilene, Pyribenzamine Ethylene diamine (EDA or en), or 1,2-diaminoethane, is an organic compound from the amines group. ... Chloropyramine is a classical (old or first generation) antihistamine drug approved in some Eastern European countries for the treatment of allergic conjuctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. ... Methapyrilene is a pyridine antihistamine. ... Tripellenamine (Pyribenzamine) is a first generation antihistamine. ...

Phenothiazine derivatives:

Alimemazine, Hydroxyethylpromethazine, Isothipendyl, Mequitazine, Methdilazine, Oxomemazine, Promethazine Phenothiazines are the largest of the 5 main classes of antipsychotic drugs. ... Mequitazine is an antihistamine. ... Methdilazine is an antihistamine. ...

Piperazine derivatives:

Buclizine, Cetirizine, Chlorcyclizine, Cinnarizine, Cyclizine, Hydroxyzine, Levocetirizine, Meclozine, Niaprazine, Oxatomide Basic piperazine structure Piperazine is a six-sided organic ring compound containing two opposing nitrogen atoms (see image). ... Buclizine is an antihistamine of the piperazine derivative family. ... Cetirizine hydrochloride is a medication used for the treatment of allergies, hay fever, angioedema, and hives. ... This article belongs in one or more categories. ... Cinnarizine is an anti histaminic drug which is mainly used for the contol of vomiting due to motion sickness. ... Cyclizine is an antihistamine drug used to treat nausea, vomiting and dizziness associated with motion sickness, vertigo and post-operative following administration of general anaesthesia and opioids. ... Hydroxyzine is a piperazine derivative that is used as an antihistamine (especially for itches), anti-emetic (nausea reducing), and anxiolytic (anxiety reducing) drug. ... Levocetirizine (as levocetirizine dihydrochloride) is a third generation non-sedative antihistamine, developed from the second generation antihistamine cetirizine. ... Meclizine (proposed INN is meclozine) is an antihistamine, considered to be an antiemetic. ... Niaprazine (Nopron) is a piperazine derivative drug which acts as a sedating antihistamine. ... Oxatomide is a piperazine antihistamine. ...

Others for systemic use:

Acrivastine, Antazoline, Astemizole, Azatadine , Azelastine, Bamipine, Cyproheptadine, Deptropine, Desloratadine, Ebastine, Epinastine, Ketotifen, Loratadine, Mebhydrolin, Mizolastine, Phenindamine, Pimethixene, Pyrrobutamine, Rupatadine, Terfenadine, Triprolidine Systemic Relating to, or affecting a particular body system; especially the nervous system. ... Acrivastine is a medication used for the treatment of allergies and hay fever. ... Astemizole is a second generation antihistamine that has a long duration of action. ... Azatadine is an antihistamine. ... Azelastine hydrochloride is an antihistamine and mast cell stabilizer available as a nasal spray (Astelin®) for hay fever and as eye drops (Optilar®) for allergic conjunctivitis. ... Periactin® (cyproheptadine hydrochloride) is an antihistaminic and antiserotonergic agent. ... Desloratadine is a drug used to treat allergies. ... Ebastin is non sedating H1 antihistamine Does not penetratethe blood brain barrier and thus allow an effective blocked of H1 receptor in peripheral tissue without centeral side effect i. ... Epinastine hydrochloride (Elestat®) is an antihistamine that is used in eye drops to treat allergic conjunctivitis. ... Ketotifen fumarate (Zaditor®) is an H1-antihistamine available in two forms. ... Loratadine is a drug used to treat allergies. ... Mebhydroline is an antihistamine. ... Rupatadine is a new selective histamine H1 receptor and platelet-activating factor (PAF) antagonist. ... Terfenadine is an antihistamine formerly used for the treatment of allergic conditions. ... Triprolidine hydrochloride is an over-the-counter antihistamine. ...

For topical use:

Bamipine, Chloropyramine, Chlorphenoxamine, Clemastine, Dimetindene, Diphenhydramine, Isothipendyl, Mepyramine , Promethazine, Thenalidine In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... Chloropyramine is a classical (old or first generation) antihistamine drug approved in some Eastern European countries for the treatment of allergic conjuctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. ... Clemastine is an over-the-counter antihistamine sold in the United States under the name Tavist. ... Diphenhydramine hydrochloride (trade name Benadryl®, as produced by Pfizer or Dimedrol outside the US) is an over-the-counter (OTC) antihistamine and sedative. ...

Antiallergic agents
excluding corticosteroids
:

Antazoline, Azelastine , Fexofenadine This article or section does not cite its references or sources. ... In physiology, corticosteroids are a class of steroid hormones that are produced in the adrenal cortex. ... Azelastine hydrochloride is an antihistamine and mast cell stabilizer available as a nasal spray (Astelin®) for hay fever and as eye drops (Optilar®) for allergic conjunctivitis. ... Fexofenadine hydrochloride (brand names include Allegra® and Telfast®) is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. ...

Other antiallergics:

Emedastine, Epinastine, Ketotifen, Olopatadine Emedastine difumarate (Emadine®) is an antihistamine used in eye drops to treat allergic conjunctivitis. ... Epinastine hydrochloride (Elestat®) is an antihistamine that is used in eye drops to treat allergic conjunctivitis. ... Ketotifen fumarate (Zaditor®) is an H1-antihistamine available in two forms. ... Olopatadine hydrochloride is an antihistamine and mast cell stabilizer, usually sold as a prescription eye drop (0. ...


  Results from FactBites:
 
Promethazine (PIM 439) (6795 words)
Promethazine is metabolized principally to promethazine sulphoxide and to a lesser degree desmethylpromethazine.
Promethazine rapidly crosses the blood brain barrier and it is thought that the sedative effects of antihistamines are due to blockade of H1 receptors in the brain (Quach et al., 1979).
Promethazine is unstable in aqueous and organic solvents (Meaking et al., 1978) and, due to its large volume of distribution, is present in very low concentrations in body fluids.
Parkinsn's List Drug DataBase promethazine HCL / Phenegran (2347 words)
Although promethazine is classified as a phenothiazine, its ability to antagonize dopamine is approximately one-tenth that of chlorpromazine.
Promethazine is classified as pregnancy category C. Antihistamines generally are not recommended for use in pregnancy, especially during the third trimester, because there is a risk of seizures in the fetus, although promethazine may be used as a sedative during labor.
Promethazine is extensively metabolized in the liver, hepatic impairment may lead to a decrease in metabolism, a subsequent increase in drug levels, and an added risk of toxicity.
  More results at FactBites »


 

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